3-Bromocyclohex-2-enone → 3-(Quinolin-6-yl)cyclohex-2-enone

HRID 1675510Notes

Reaction equation

HRID 1675510 reaction equation
Br[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)O1>>[N:23]1[C:24]2[C:19](=[CH:18][C:17]([C:2]3[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=3)=[CH:26][CH:25]=2)[CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 109650383-Bromocyclohex-2-enoneHCID 162177846-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

Product 1

HCID 252344123-(Quinolin-6-yl)cyclohex-2-enoneYield 88%

Procedure

Synthesized from 3-bromocyclohex-2-enone and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography using gradient elution (40 to 100% ethyl acetate/hexanes) yielded the product (164 mg, 88%) as a white powder. 1H NMR (CDCl3, 300 MHz): δ 8.92 (dd, J=4.2, 1.5 Hz, 1H), 8.17 (d, J=7.8 Hz, 1H), 8.11 (d, J=9.0 Hz, 1H), 7.95 (d, J=2.1 Hz, 1H), 7.86 (dd, J=9.0, 2.4 Hz, 1H), 7.43 (dd, J=8.4, 4.5 Hz, 1H), 6.54 (s, 1H), 2.89 (t, J=6.3 Hz, 2H), 3.53 (t, J=6.3 Hz, 2H), 2.21 (pent, J=6.3 Hz, 2H). 13C NMR (CDCl3, 75 MHz): δ 199.4, 158.3, 151.2, 148.6, 136.7, 136.5, 129.9, 127.8, 126.8, 126.3, 125.7, 121.7, 37.3, 28.2, 22.8. LCMS (ESI): mass calcd for (C15H13NO) m/z 223.10; measured [M+H]+: m/z 224.80.

Workup

  1. customPurification by automated flash chromatography
  2. washelution (40 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-995bc91f59054dc8b1949e9efe68360a
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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